Conversion of distillation residues to useful metal working lubricants

ABSTRACT

Residues resulting from the distillation of fatty acids obtained from fat-splitting processes are converted by the process of this invention to useful metal working lubricants. The present process utilizes distillation residues, which are typically viscous oils ranging in color from dark brown to black and which heretofore had little or no commercial value and were burned or otherwise disposed of, to produce lubricants having performance characteristics which make them suitable for use in continuous metal-casting and other metal working operations.

Sturwold et al.

Dec. 2, 1975 CONVERSION OF DISTILLATION RESIDUES TO USEFUL METAL WORKING LUBRICANTS Inventors: Robert J. Sturwold; Fred 0.

Barrett; Walter E. Utz, all of Cincinnati, Ohio Assignee: Emery Industries, Inc., Cincinnati,

Ohio

Filed: Aug. 8, 1974 Appl. No.: 495,620

US. Cl. 252/56 S; 72/42; 252/56 R Int. CL C10M l/24; CIOM 3/18; ClOM 5/12;

ClOM 7/20 Field of Search 72/42; 252/56 R, 56 S References Cited UNITED STATES PATENTS 11/1972 Baldwin 252/56 S 3,778,454 12/1973 Kleiman et a1 252/56 'R Primary Examiner Delbert E. Gantz Assistant Examinerl. Vaughn Attorney, Agent, or FirmGerald A. Baracka; John D.

Rice

[57] ABSTRACT Residues resulting from the distillation of fatty acids obtained from fat-splitting processes are converted by the process of this invention to useful metal working lubricants. The present process utilizes distillation residues, which are typically viscous oils ranging in color from dark brown to black and which heretofore had little or no commercial value and were burned or otherwise disposed of, to produce lubricants having performance characteristics which make them suitable for use in continuous metal-casting and other metal working operations.

10 Claims, N0 Drawings CONVERSION OF DISTILLATION RESIDUES TO USEFUL METAL WORKING LUBRICANTS BACKGROUND OF THE INVENTION The present invention is directed to a process for converting waste residues obtained from the distillation of fatty acids produced in fat-splitting operations wherein fats and fatty oils are hydrolyzed into fatty acids and glycerol by subjecting the fatty materials to high temperatures and pressures in the presence of water. Fat-splitting processes are well-known and widely used industrially to obtain fatty acids and glycerine.

The fatty acids obtained from such splitting operations, in addition to being gross mixtures containing numerous fatty acids, typically have poor color and odor due to the presence of a variety of impurities resulting from the severe processing conditions and impurities in the fatty material being treated. In view of this, it is customary to distill the resulting fatty acid mixtures for purification purposes and/or to separate the various fatty acid components. This is accomplished using conventional distillation equipment and procedures. At the completion of the distillation there is a residue consisting primarily of oxidative and polymeric by-products including color bodies, odor bodies, modified glycerides and unhydrolyzed or partially hydrolyzed fatty materials. This residue, in some instances is subjected to further pressure splitting, however, even when one or more additional splitting steps are employed a final distillation residue will still be obtained.

These oily malodorous distillation residues are highly colored, ranging in color from deep brown to totally black. In the past, it has been the usual practice in industrial operations to dispose of these residues by buming, burying, etc., but because of there low fuel value and for ecological reasons this is becoming increasingly more difficult and costly. These residues have also been suggested for use as extenders in tar products but there is limited use in this area.

SUMMARY OF THE INVENTION We have now discovered a process whereby waste distillation residues are converted to useful metal working lubricants. The process simply involves contacting the residue with a hydroxylic compound containing at least one hydroxyl group and a least four carbon atoms at a temperature above 100C, preferably between 150 and 250C, while removing water from the reaction mixture. The reaction is continued until the acid value is less than 10, and more preferably, 5 or below.

vThe equivalents ratio of the hydroxylic compound to the residue will be 1:1 or higher, based on the acid value of the residue. Residues employed are obtained when fatty acids produced in fat-splitting processes are distilled and typically are brown to black liquids having 180F kinematic viscosities in the range 40-300 centistokes with iodine values from about 50 to 100, acid values between about 50 and 100 and saponification values between about 100 and 200. Hydroxylic compounds useful in the process are aliphatic, cycolaliphatic and aromatic and mono-, diand polyhydric alcohols containing 6 to 20 carbon atoms and polyoxyalkylene glycols having molecular weights from about 100 to 4000. The products of this invention may be used as such or filtered with diatomaceous earth. While these products may vary in composition and lubrication properties, they preferably have an acid value of 5 or less, flash points above 500C and fire points greater than 540 C. The products of this invention are useful in a variety of lubrication applications, however, they 5 find particular utility as lubricants for the continuous casting of metals such as steel or steel alloys.

DETAILED DESCRIPTION This invention provides a process for converting waste residues resulting from the distillation of certain fatty acids to useful products, namely, metal working lubricants. The distillation residues employed herein result from fat-splitting processes wherein fats and fatty oils are hydrolyzed into fatty acids and glycerol at high temperatures and pressures in the presence of water. Thee so-produced fatty acids upon distillation yield the waste residue.

The manner in which the fat-splitting process and fatty acid distillation are conducted does not form a part of this invention but serve only as a source for the material to be processed. In other words, the present process is useful with any distillation residue without regard to the conditions employed during the fat-splitting operation and subsequent distillation. Known fatsplitting procedures, such as those described in US. Pat. Nos. 2,156,863 and RE 22,006, and various modifications thereof used by industry can be employed. A typical industrial fat-splitting operation, for example, involves countercurrent contact of fat and water in a column. This is accomplished by introducing the fatty material into the column under high pressure through a sparge ring which breaks the fat into small droplets. As the fat droplets are heated they pass upward through the column where the temperature is increased by the introduction of steam under high pressure. Water is charged under pressure through a sparge ring at the top of the column. The rate of flow of fat and water are carefully controlled to permit maximum contact with each other. The column is completely filled with liquids and vaporization of water is prevented be maintaining the pressure within the system in excess of the vapor pressure of water at the operating temperature. Generally, the pressure will range between about and 1,600 psi while maintaining a temperature of at least 350F and, more preferably, between about 365F and 600F. Sweet water (aqueous glycerine) is collected at the bottom of the column and pumped to a glycerine concentrator. Fatty acids are discharged from the top of the tower.

Fatty acids originating from the fat-splitting operation are highly colored and contain a van'ety of impurities. It is customary therefore to distill the fatty acids either solely for the purpose of purification distillation or additionally to separate the various acids of different chain lengths and boiling points. The distillation can be conducted eitheras a batch process or continuously. Continuous distillation is preferred since losses are minimized and it is possible to increase the yield and quality of the distilled products and decrease the time of exposure of the acids to high temperatures. Typically, a continuous commercial fatty acid distillation process involves initially stripping the fatty acids to remove light ends and odor bodies and then pumping the bottoms from the stripper column into the main fractionation column fitted with a plurality of bubblecap or other suitable trays. The residue (bottoms) of the main column may be used directly in the process of this invention or may be fed to another stripping tower wherein very high boiling fatty acids are removed and the residue remaining after this step used in this process. Still another alternative would be to subject either of the so-obtained residues to a second splitting and distillation operation, following the same general procedure as outlined above, and to convert the residue to useful metal working lubricants in accordance with the invention. By subjecting the residues to additional splitting it is possible to improve the yield of fatty acids and glycerine. It is not generally practical, however, to have more than two splitting operations in the treatment of fatty materials since only marginal improvements are possible after two splittings. In all cases, however, a residue will be obtained from the distillation of the fatty acids which quite unexpectedly is converted by the process of this invention to a useful metal working lubricant. Similarly, if a batch distillation procedure is employed the pot residue remaining after removal of the fatty acids can be utilized for the process of this invention.

Residues useful for the present process are those obtained by splitting any of the commonly employed materials followed by distillation in the above manner. Common fatty materials which are split to obtain fatty acids and glycerine include vegetable and animal oils, such as tallow and other related greases, coconut oil, soybean oil, corn oil, peanut oil, cottonseed oil and the like. In some instances it may be advantageous to hydrogenate the fatty material prior to splitting.

The waste distillation residues which are converted to useful lubricant products by this process are mixtures containing numerous oxidative and polymeric byproducts including modified glycerides, unhydrolyzed and partially hydrolyzed fatty materials and color and odor bodies and the precise composition is difficult and, in most instances impossible, to completely define.

While the chemical makeup will vary depending on the fatty material used, splitting conditions and distillation procedure, the residues are in all instances highly colored (dark brown black) liquids having 180F kinematic viscosities ranging from 40 to 300 centistokes. The residues typically have iodine values from about 50 to 100, acid values between 50 and 100 and saponification values from 100 to 200. While the content of unsaponafiable materials in the residue can range up to about 50% by weight it is more usually less than about 25%.

The above-described residues, which as such have little or no practical or commercial value, are converted to useful lubricants in accordance with the process of the invention by contacting with hydroxylic compounds at elevated temperatures until a low acid value is obtained. The process is conducted at temperatures above 100C in order that the water formed during the reaction can be removed from the system. Best results are obtained at temperatures between about 150 and 250C and, more preferably, between about 180 and 230C. It is not necessary that a catalyst be employed to promote the condensation, however, known esterification catalysts such as sulfuric acid, alkyl and aryl sulfonic acids such as p-toluene sulfonic acid, sodium acid sulfate, phosphoric acid, stannous oxalate condensed butyl titanate, or the like can be used. Also, it is possible in carrying out the reaction to employ an organic diluent which is inert to the reaction conditions employed but which preferably will form an azeotrope with water. Xylene and toluene are suitable diluent/carriers for this purpose. The reaction is continued until the reaction mixture has a low acid value, that is, the acid value has been lowered to about 10 orv below. Excellent results are obtained when the acid value is 5 or less.

Hydroxylic compounds useful in the present process contain one or more free hydroxyl groups and at least four carbon atoms. Suitable hydroxylic compounds include the aliphatic, cycloaliphatic, aromatic and polyoxyether alcohols, including mono-, di and polyhydric alcohols and mixtures thereof. Especially useful hydroxylic compounds for this invention are aliphatic, cycloaliphatic and aromatic mono-, di and polyhydric alcohols containing six to 20 carbon atoms and polyoxyalkylene glycols having molecular weights from about to 4000. Useful monohydric alcohols, include nbutyl alcohol, amyl alcohol, isoamyl alcohol, n-hexyl alcohol, 2-ethylbutyl alcohol, n-octyl alcohol, 2-ethylhexyl alcohol, decyl alcohol, lauryl alcohol, oleyl alcohol, ethylene glycol mono-n-butyl ether, diethyleneglycol mono-n-butyl ether, diethyleneglycol mono-2- ethylhexyl ether, propyleneglycol mono-n-butyl ether, dipropyleneglycol mono-methyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropyleneglycol mono-isopropyl ether, cyclohexanol, benzyl alcohol, oxo alcohols, such as isoctyl, isodecyl and tridecyl alcohols, and the like. Diand polyhydric alcohols, including polyoxyether alcohols, which can be used include l,4-butanediol, 1,5- pentanediol, l,6-hexanediol, 1,8-octanediol, 1,10- decanediol, 1,4-cyclohexanedimethanol, glycerol, sorbitol, pentaerythritol, trimethylolethane, trimethylolpropane, diethyleneglcyol, dipropyleneglycol, tripropyleneglycol and similar materials having higher degrees of polymerization such as polyethylene glycols, polypropylene glycols, polybutylene glycol and poly(ethylenepropylene) glycols.

In carrying out the process a stoichiometric amount (1:1 equivalents ratio) of hydroxylic compound, based on the acid value of the residue, can be used or the hydroxylic material can be present in excess. The only requirement as to the amount of mono-, di or polyhydric alcohol used for the process is thatsufficient hydroxyl groups be present for reaction (to react with the acid groups) to reduce the acid value of the product to about 10 or below. As a practical matter when using hydroxylic materials which are not readily removable from the reaction mixture at the end of the reaction, that is, having a boiling point above about C at 1 mm Hg, the stoichiometry is strictly observed and no more than about 5% excess of the alcohol should be charged. With the lower boiling and more volatile alcohols (such as monohydric alcohols) where it is possible to readily strip the materialsfrom the reaction mixture, an excess can be employed which helps drive the reaction to completion. Some unreacted alcohol may be present in the final product without unduly detracting from the desirable properties.

Other variations in the process of this invention are possible as will be recognized by those skilled in the art. For example, it is possible to modify the lubricant properties, as well as other properties, of the resulting product by including other carboxylic materials in the reacw gonic acid, lauric acid, palmitic acid, stearic acid, oleic acid, azelaic acid, sebacic acid, succinic acid, glutaric brassylic acid, malonic acid, fumaric acid, aconitic acid and dimer and trimer acids containing 32 to 54 carbon atoms, which are the polymerization products of unsatsphere of nitrogen with continuous stirring at about 220C for approximately 4 hours during which time about 9 mls of water were removed. When the acid value of the reaction mixture was less than 10 a vaccum urated monocarboxylic acids. The addition of dimer 5 of about 1 torr was applied to remove any additional acid is particularly useful to enhance the lubricant water of reaction and the excess 2-ethylhexanol. The properties of the product whereas with azelaic acid and resulting dark product had a viscosity of 26.2 centisebacic acids the solubility characteristics can be markstokes at 180F and other properties making it useful as edly altered, particularly when the hydroxylic coma metal working lubricant. pound is polyoxyethylene glycol. 10

The product obtained from the above-described pro- EXAMPLE H cess can be used directly if stiochiometric amounts of Using a procedure similar to that described in Examthe hydroxylic compound have been employed, otherple I, the residue obtained when a first fatty acid distilwise the excess mono-, di or polyhydric alcohol will be lation residue is subjected to a second splitting operastripped from the product at the termination of the retion and fractional distillation was reacted with benzyl action. This is accomplished by heating while the pres alcohol. The residue had the following properties: sure is lowered to about 1 mm Hg. While it is not necessary, it is often advantageous to filter the product at the Add value 80 termination of the reaction using diatomaceous earth. sappnificalion value 164 Any of the commonly used and commercially available i g li glgg Z2 diatomaceous earths (often referred to as diatomite or 180F viscosities 122 centistokes kieselguhr) obtained from natural deposits and comprised Primarily of silica l h Suitable 9 Benzyl alcohol was employed in excess based on a thls P P By Such filtratlhh 1t posslhle to obtehn calculated equivalent weight of 750 for the residue. more uniform and consistent products WhlCh are easily 25 The reaction mixture was maintained between PP to metalsand 220C for about 10 hours during which time the Acld values of the Products be about 9 or theoretical amount of water was removed. A vacuum low. Superior results are obtained when the acid value was then applied to the System and heating continued is 5 or below. The products are further characterized as at 225C to remove the final traces of water and Strip havhg flash Pomts above about 500C and fire PF off the unreacted (excess) benzyl alcohol. About 0.5 greater than ahoht 540C The Products have lubnc" wt. Dicalite (a commercially available diatomaceous measured the Pale) T Method (ASTM D earth filter aid) was added and the reaction mixture fil- 2670), comparable to soybean Oll, cramb 011 and 1 tered. The final product had an acid value of about 8 seed oil without having certain undesirable properties and a viscosity of 260 centistokes at 0 generally attributed to these natural oils.

The following Examples serve to illustrate the inven- EXAMPLE III VI tion more y; f they are e d solely for A series of experiments was conducted in accordance the P p (fflhhstrahoh and hot as a hmltahon on the with the process of this invention wherein the distilla- Scope of the lhvehhoh- Ih mese exampl es all Parts and tion residue of Example 11 was reacted with various P are e n 9 a welght h 40 polyhydric alcohols. The alcohols employed were neowr se rndlcated. Vlscosrtres are kinematic vlscosrtres obpentyl glycol, t imethylolpropane, trimethylolethane tamed accordance wlth ASTM D and pentaerythritol. In all these experiments the equivues and hydroxyl values reported as KOH/gram are alents ratio of alcohol to residue was 1.0: 1 .0 and the redetermihed by ASTM D 198O'67 and ASTM D action mixtures were heated (200220C) until the 1957-63, respective]! acid value was less than 9. Reaction times ranged from EXAMPLE I 6 to 10 hours. The following table lists the polyhydric glycol used for each of the preparations, the amount A glass reactor eqhlpped Wlth a thermometer (grams) of the alcohol and the residue charge, and the nitrogen inlet and water trap topped wlth cooled viscosities and pour points of the resulting products.

Example No. III IV V VI Alcohol neopentyl trimethyloltrimethylolpentaerythritol glycol propane ethane Reactant charge 64.8/93/5 56.3/943.7 48/900 43.4/956.6 (alcohol/residue) 180F Viscosity 118 259 264 489 (centistokes) Pour point (F) 0 20 15 35 (ASTM D 97-57) All of the above products were filtered with a diatomaceous earth filter aid and were useful lubricants.

The above examples clearly demonstrate that a variety of useful products are obtained by treating residues resulting from the distillation of fatty acids produced by pressure splitting fatty materials. It is truly surprising that waste distillation residues, heretofore, considered to have little or no practical or commercial value, are converted by the process of this invention to products as lubricants for continuous casting operations and other metal working applications. That acceptable lubrication can be obtained from these undesirable appearing wastes is by itself truly surprising, however, it is even more remarkable when one considers that the products of this process can be used without further purification.

To demonstrate the effectiveness of the products of this invention as lubricants they were evaluated with a Falex machine. This machine provides a convenient and reliable means of determining the film strength or load carrying properties of materials as extreme pressures are applied. Falex testing is recognized throughout the industry as a means of measuring the relative effectiveness of various lubricants. For the Falex wear test (ASTM D 2670-67) a 60 gram sample of the product is placed in the cup and positioned in the machine so that the steel pin and blocks are completely immersed in the sample. The loading device is attached, the machine started and the load increased to 350 pounds and run for minutes. After this time the load is further increased to 800 pounds and maintained for minutes. Readings are taken at the beginning and end of the 15 minute period and the difference in the readings reported as the units of wear. The following table sets forth the test results obtained when the products of Examples I-VI were evaluated in the Falex test. In addition to the wear tests data, other significant lubricant properties including viscosities of the product at l00F and 2l0F and the flash and fire points are provided.

PRODUCT OF EXAMPLES I II III IV V VI Units of Wear l 76 49 1 4 Viscosity 100F 129 130 858 2025 2170 4750 210F 17.3 17.5 68.5 133 142 263 Flash point (*F) 510 525 575 575 585 570 Fire point (F) 555 590 605 600 590 EXAMPLE VII To further demonstrate the versatility of the present process and the ability to obtain useful lubricant products using mixed alcohols an experiment was conducted wherein 407 parts of the residue of Example II, 4.2 parts neopentyl glycol and 88.3 parts 2-ethylhexanol excess) were reacted. Stannous oxalate (0.03%) was used to promote the reaction. After about 14 hours (220C) an acid value of 3.8 was obtained. At this point the vacuum was further reduced and about 18 parts 2-ethylhexanol stripped from the reaction mixture. The final product (acid value 4.0) was recovered by filtration with a diamomaceous earth filtering agent. The product had 100F and 210F viscosities of 104 centistokes and l4.5 centistokes, respectively, a flash point of 500F and a tire point of 535F. In the Falex test, following the procedure set forth above, there was no measurable wear using the product of this Example.

EXAMPLE VIII That additional advantages are possible employing the process of this invention isevident from the following example wherein a lubricant product, emusifiable with water without the addition of external emulsifying agents, was prepared from the distillation residue of Example II. To prepare this self-emulsifiable product polyoxyethylene glycol (average molecular weight of 400) and 2-ethylhexanol were reacted with the residue at an equivalent ratio of 0.2:0.8:1.0, respectively. 0.03 Percent condensed butyl titanate was employed to catalyze the reaction which was carried out at 2l0-220C for about 30 hours, until an acid value of 3.4 was obtained. The recovered product had a F viscosity of 118 centistokes, 210F viscosity of 17.0 centistokes, 315F smoke point, 495F flash point and 545F fire point. In the Falex wear test, there was no measurable wear when the product of this Example was used as the neat oil and only 2 units wear when a 5% Aqueous emulsion product was tested. In addition to the excellent wear test properties obtained with the emulsion, the emulsions were quite stable and very readily formed. A 5% aqueous emulsion was also prepared from the product of Example I using ethoxylated nonylphenol as the emulsifier and gave 22 units wear in the Falex test.

The above products are useful as lubricants in a variety of metal working operations including, for example, forging, hot pressing, blanking, bending, stamping, drawing, cutting, punching, drilling, and the like, however, they find particular utility as lubricants for continuous casting of molten metals. These lubricants greatly improve metal working operations in that they prevent sticking of metal pieces, decrease wear of dyes and cutting bits and lower the power requirements for the operation by reducing friction. The lubricants are readily substitutable for, or can be used in combination with, any of the commonly used industrial lubricants including vegetable, animal, mineral and petroleum oils and, in most cases, provide distinct advantages over the aforementioned oils.

The products of this invention are suitable for use with both ferrous and non-ferrous metals. They can be used with steel and various alloys, such as brass and bronze, aluminum, copper, titanium and other metals. They are especially useful with steel and steel alloys, particularly, in continuous casting operations involving these metals. In this type of operation molten steel is poured into a suitable mold and continuously cast into billets or slabs. Lubricants are necessary to facilitate heat transfer and prevent sticking of the metal to the mold to insure continuous and uniform flow of the metal. While mineral oils and various natural oils including rapeseed oil, crambe oil, castor oil, cottonseed oil and soybean oil have typically been used by the industry, there are certain disadvantages associated with the use of these oils. Mineral oils tend to burn too readily and produce excessive amounts of smoke which makes it impossible to maintain visual contact with the mold. The vegetable oils, which all suffer common drawbacks of limited supply and rising prices, have been the most widely used lubricants for this purpose. Rapeseed oil and crambe oil are particularly effective and in some cases are mixed with a higher viscosity mineral oil. The vegetable oils, however, upon decomposition produce excessive amounts of acrolein, which has a very disagreeable choking odor, causes considerable irritation to the eyes, and in sufficient concentration is potentially dangerous to mill personnel. Most of these oils have the added disadvantage of being susceptible to oxidation and form a coating (varnish) on the mold which requires that the mold be periodically cleaned resulting in considerable and costly downtime.

While the products of this invention find utility in numerous applications where lubricants are required they are particularly useful as lubricants in the continuous casting of steel and eliminate many of the difficulties encountered with the heretofore used lubricants. The present products have sufficiently low viscosities so that they flow easily, are readily pumpable and can be applied using conventional application methods to form a uniform and continuous film between metal and mold, which is essential for efficient operation of the process and the obtainment of slabs and billets substantially free of surface defects. Another desirable feature of the products is their ability to burn without generating excessive amounts of smoke and soot and without depositing unduly large amounts of carbonaceous matter on the steel. Still more advantageous is the fact that with these products acrolein formation is minimized or completely eliminated. Also, these products exhibit excellent oxidative stability which eliminates problems generally associated with the storage and use of natural oils and minimizes varnish formation on the mold and surface of the metal.

Numerous modifications of the process and the products obtained thereby will be evident to those skilled in the art are are within the scope of the invention. For example, the viscosity, fire point, flash point, pour point, etc. can be widely varied by judicious selection of the polyhydric compound or by the inclusion of other materials. Products obtained from this process may be mixed with other oils including mineral oil and other synthetic or natural lubricants. Additives may be incorporated into the product either be blending after the process is completed or by including in the process, if the additives do not interfere with the product forma- 10 tion. Additives may be useful for a variety of purposes and may be present in small amounts or form a substantial portion of the formulated lubricant.

We claim:

1. A process for converting residues, obtained when fatty acids produced from fat-splitting processes are distilled, to useful lubricants which comprises contacting the residue with a hydroxylic compound containing at least one hydroxyl group and at least four carbon atoms at a temperature above C while removing water from the reaction mixture until the acid value of the product is about 10 or below, the equivalents ratio of said hydroxylic compound to said residue being 1:1 or higher, based on the acid value of the residue.

2. The process of claim 1 wherein the residue has an iodine value from about 50 to 100, an acid value between about 50 and 100 and a saponification value between 100 and 200.

3. The process of claim 1 wherein the temperature is maintained between about and 250C and the hydroxylic compound is selected from the group consisting of aliphatic, cycloaliphatic and aromatic, mono-, diand polyhydric alcohols containing six to 20 carbon atoms and polyoxyalkylene glycols having molecular weights from about 100 to 4,000.

4. The process of claim 3 conducted to an acid value of 5 or below and wherein the temperature is between about 180 and 230C.

5. The process of claim 3 wherein the reaction product is treated with diatomaceous earth and filtered.

6. The composition prepared by the process of claim 1.

7. The composition prepared by the process of claim 3.

8. The composition of claim 7 which is further characterized by having an acid value of 5 or below, a flash point above 500C and a fire point greater than 540C.

9. The composition of claim 8 wherein the hydroxylic compound is 2-ethylhexanol.

10. The composition of claim 8 wherein the hydroxylic compound is isodecyl alcohol.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,923,702 Dated December 2, 1975 l v t R. J. Sturwold, F. O. Barrett and W. E. Utz

It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Column 1, line 37, "there" should read their Column 2, line 53, delete distillation Column 5, line 30, "C" should read P Column 5, line 31, "C" should read F Column 6, line 4, "vaccum" should read vacuum Column 6, line 22, "viscosities" should read viscosity Column 7, line 2, after products insert useful Column 7, line 31, "tests" should read test Column 9, line 33, the first "are" should read and Signed and Scaled this first Day of June1976 [SEAL] Atlest:

RUTH c. msou c. MARSHALL DANN Atmm'ng Officer Commissioner oj'Parems and Trademarks 

1. A PROCESS FOR CONVERTING RESIDUES, OBTAINED WHEN FATTY ACIDS PRODUCED FROM FAT-SPLITTING PROCESSES ARE DISTILLED, TO USEFUL LUBRICANTS WHICH COMPRISES CONTACTING THE RESIDUE WITH A HYDROXYLIC COMPOUND CONTAINING AT LEAST ONE HYDROXYL GROUP AND AT LEAST FOUR CARBON ATOMS AT A TEMPERATURE ABOVE 100*C WHILE REMOVING WATER FROM THE REACTION MIXTURE UNTIL THE ACID VALUE OF THE PRODUCT IS ABOUT 10 OR BELOW, THE EQUIVALENTS RATIO OF SAID HYDROXYLIC COMPOUND TO SAID RESIDUE BEING 1:1 OR HIGHER, BASED ON THE ACID VALUE OF THE RESIDUE.
 2. The process of claim 1 wherein the residue has an iodine value from about 50 to 100, an acid value between about 50 and 100 and a saponification value between 100 and
 200. 3. The process of claim 1 wherein the temperature is maintained between about 150* and 250*C and the hydroxylic compound is selected from the group consisting of aliphatic, cycloaliphatic and aromatic, mono-, di- and polyhydric alcohols containing six to 20 carbon atoms and polyoxyalkylene glycols having molecular weights from about 100 to 4,000.
 4. The process of claim 3 conducted to an acid value of 5 or below and wherein the temperature is between about 180* and 230*C.
 5. The process of claim 3 wherein the reaction product is treated with diatomaceous earth and filtered.
 6. The composition prepared by the process of claim
 1. 7. The composition prepared by the process of claim
 3. 8. The composition of claim 7 which is further characterized by having an acid value of 5 or below, a flash point above 500*C and a fire point greater than 540*C.
 9. The composition of claim 8 wherein the hydroxylic compound is 2-ethylhexanol.
 10. The composition of claim 8 wherein the hydroxylic compound is isodecyl alcohol. 